Correct me if im wrong on this, but I believe the only way to do that is for your employer to cut a separate check or deposit it into a HSA account? From there anything spent on medical expenses is tax free.

I am not familiar with how HSA's operate but I would like to know how to handle the situation I had mentioned. My employer is kicking around the idea of just giving employees a certain amount of money. At some point I assume a lot of employers are going to just give people a set amount of money.

here is wikipedia on an HSA. It also goes on to mention the yearly limit for family is $6500, which isn't enough for many family plans.

"A health savings account (HSA) is a tax-advantaged medical savings account available to taxpayers in the United States who are enrolled in a high-deductible health plan"